JP4261855B2 - Phenanthroline compound and organic light emitting device using the same - Google Patents
Phenanthroline compound and organic light emitting device using the same Download PDFInfo
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- JP4261855B2 JP4261855B2 JP2002272408A JP2002272408A JP4261855B2 JP 4261855 B2 JP4261855 B2 JP 4261855B2 JP 2002272408 A JP2002272408 A JP 2002272408A JP 2002272408 A JP2002272408 A JP 2002272408A JP 4261855 B2 JP4261855 B2 JP 4261855B2
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- light emitting
- layer
- organic light
- emitting device
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- -1 Phenanthroline compound Chemical class 0.000 title claims description 40
- 150000002894 organic compounds Chemical class 0.000 claims description 16
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
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Images
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
- H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
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Description
【０００１】
【発明の属する技術分野】
本発明は、新規な有機化合物およびそれを用いた有機発光素子に関する。
【０００２】
【従来の技術】
有機発光素子は、陽極と陰極間に蛍光性有機化合物または燐光性有機化合物を含む薄膜を挟持させて、各電極から電子およびホール（正孔）を注入することにより、蛍光性化合物または燐光性化合物の励起子を生成させ、この励起子が基底状態にもどる際に放射される光を利用する素子である。
【０００３】
１９８７年コダック社の研究（非特許文献１）では、陽極にＩＴＯ、陰極にマグネシウム銀の合金をそれぞれ用い、電子輸送材料および発光材料としてアルミニウムキノリノール錯体を用い、ホール輸送材料にトリフェニルアミン誘導体を用いた機能分離型２層構成の素子で、１０Ｖ程度の印加電圧において１０００ｃｄ／ｍ2程度の発光が報告されている。関連の特許としては，特許文献１〜３等が挙げられる。
【０００４】
また、蛍光性有機化合物の種類を変えることにより、紫外から赤外までの発光が可能であり、最近では様々な化合物の研究が活発に行われている。例えば、特許文献４〜１１等に記載されている。
【０００５】
近年、燐光性化合物を発光材料として用い、三重項状態のエネルギーをＥＬ発光に用いる検討が多くなされている。プリンストン大学のグループにより、イリジウム錯体を発光材料として用いた有機発光素子が、高い発光効率を示すことが報告されている（非特許文献２）。
【０００６】
さらに、上記のような低分子材料を用いた有機発光素子の他にも、共役系高分子を用いた有機発光素子が、ケンブリッジ大学のグループ（非特許文献３）により報告されている。この報告ではポリフェニレンビニレン（ＰＰＶ）を塗工系で成膜することにより、単層で発光を確認している。
【０００７】
共役系高分子を用いた有機発光素子の関連特許としては、特許文献１２〜１６等が挙げられる。
【０００８】
このように有機発光素子における最近の進歩は著しく、その特徴は低印加電圧で高輝度、発光波長の多様性、高速応答性、薄型、軽量の発光デバイス化が可能であることから、広汎な用途への可能性を示唆している。
【０００９】
しかしながら、現状では更なる高輝度の光出力あるいは高変換効率が必要である。また、長時間の使用による経時変化や酸素を含む雰囲気気体や湿気などによる劣化等の耐久性の面で未だ多くの問題がある。さらにはフルカラーディスプレイ等への応用を考えた場合の色純度の良い青、緑、赤の発光が必要となるが、これらの問題に関してもまだ十分でない。
【００１０】
一方、フェナントロリン化合物がその優れた電子輸送性から電子輸送材料や発光材料として用いられる。フェナントロリン化合物を有機発光素子に用いた例として、特許文献１７〜２１などが挙げられるが、発光層材料や電子輸送材料として用いた際の特性は十分なものではない。
【００１１】
【特許文献１】
米国特許第４，５３９，５０７号明細書
【特許文献２】
米国特許第４，７２０，４３２号明細書
【特許文献３】
米国特許第４，８８５，２１１号明細書
【特許文献４】
米国特許第５，１５１，６２９号明細書
【特許文献５】
米国特許第５，４０９，７８３号明細書
【特許文献６】
米国特許第５，３８２，４７７号明細書
【特許文献７】
特開平２−２４７２７８号公報
【特許文献８】
特開平３−２５５１９０号公報
【特許文献９】
特開平５−２０２３５６号公報
【特許文献１０】
特開平９−２０２８７８号公報
【特許文献１１】
特開平９−２２７５７６号公報
【特許文献１２】
米国特許第５，２４７，１９０号明細書
【特許文献１３】
米国特許第５，５１４，８７８号明細書
【特許文献１４】
米国特許第５，６７２，６７８号明細書
【特許文献１５】
特開平４−１４５１９２号公報
【特許文献１６】
特開平５−２４７４６０号公報
【特許文献１７】
特開平５−３３１４５９号公報
【特許文献１８】
特開平７−８２５５１号公報
【特許文献１９】
特開平１０−７９２９７号公報
【特許文献２０】
特開２００１−２６７０８０号公報
【特許文献２１】
特開２００１−１３１１７４号公報
【非特許文献１】
Ａｐｐｌ．Ｐｈｙｓ．Ｌｅｔｔ．５１，９１３（１９８７）
【非特許文献２】
Ｎａｔｕｒｅ，３９５，１５１（１９９８）
【非特許文献３】
Ｎａｔｕｒｅ，３４７，５３９（１９９０）
【００１２】
【発明が解決しようとする課題】
本発明の目的は、新規なフェナントロリン化合物を提供することにある。
【００１３】
また本発明の目的は、特定なフェナントロリン化合物を用い、極めて高効率で高輝度な光出力を有する有機発光素子を提供することにある。
【００１４】
また、極めて耐久性のある有機発光素子を提供することにある。
【００１５】
さらには製造が容易でかつ比較的安価に作成可能な有機発光素子を提供する事にある。
【００１６】
【課題を解決するための手段】
即ち、本発明のフェナントロリン化合物は、下記一般式［Ｉ］〜［ＩＩＩ］のいずれかで示されることを特徴とする。
【００１７】
【化８】
（式中、Ｒ1、Ｒ2、Ｒ3、Ｒ4、Ｒ5およびＲ6は、水素原子、置換あるいは無置換のアルキル基、置換あるいは無置換のアラルキル基、置換あるいは無置換のアリール基，置換あるいは無置換の複素環基またはハロゲン原子を表わし、同じであっても異なっていてもよい。Ａｒ1およびＡｒ2は、置換あるいは無置換のフルオレニル基、置換あるいは無置換のフルオランテニル基、置換あるいは無置換のペリレニル基または置換あるいは無置換のカルバゾリル基を表わし、同じであっても異なっていてもよい。）
【００１９】
【化９】
（式中、Ｒ7、Ｒ8、Ｒ9、Ｒ10、Ｒ11およびＲ12は、水素原子、置換あるいは無置換のアルキル基、置換あるいは無置換のアラルキル基、置換あるいは無置換のアリール基，置換あるいは無置換の複素環基またはハロゲン原子を表わし、同じであっても異なっていてもよい。Ａｒ3およびＡｒ4は、置換あるいは無置換のフルオレニル基、置換あるいは無置換のフルオランテニル基、置換あるいは無置換のペリレニル基または置換あるいは無置換のカルバゾリル基を表わし、同じであっても異なっていてもよい。）
【００２１】
【化１０】
（式中、Ｒ13、Ｒ14、Ｒ15およびＲ16は、水素原子、置換あるいは無置換のアルキル基、置換あるいは無置換のアラルキル基、置換あるいは無置換のアリール基，置換あるいは無置換の複素環基またはハロゲン原子を表わす。Ｒ13およびＲ14は、同じであっても異なっていてもよい。Ａｒ5、Ａｒ6、Ａｒ7およびＡｒ8は、置換あるいは無置換のフルオレニル基、置換あるいは無置換のフルオランテニル基、置換あるいは無置換のペリレニル基または置換あるいは無置換のカルバゾリル基を表わし、同じであっても異なっていてもよい。）
【００２３】
本発明のフェナントロリン化合物は、前記フルオレニル基が、下記一般式［ＩＶ］で示されることが好ましい。
【００２４】
【化１１】
（式中、Ｒ17は、水素原子、置換あるいは無置換のアルキル基、置換あるいは無置換のアラルキル基、置換あるいは無置換のアリール基、置換あるいは無置換の複素環基、置換アミノ基、シアノ基またはハロゲン原子を表わす。Ｒ18およびＲ19は、水素原子、置換あるいは無置換のアルキル基、置換あるいは無置換のアラルキル基、置換あるいは無置換のアリール基または置換あるいは無置換の複素環基を表わし、同じであっても異なっていてもよい。）
【００２６】
また、前記フルオランテニル基が、下記一般式［Ｖ］で示されることが好ましい。
【００２７】
【化１２】
（式中、Ｒ20は、水素原子、置換あるいは無置換のアルキル基、置換あるいは無置換のアラルキル基、置換あるいは無置換のアリール基、置換あるいは無置換の複素環基、置換アミノ基、シアノ基またはハロゲン原子を表わす。）
【００２９】
また、前記ペリレニル基が、下記一般式［ＶＩ］で示されることが好ましい。
【００３０】
【化１３】
（式中、Ｒ21は、水素原子、置換あるいは無置換のアルキル基、置換あるいは無置換のアラルキル基、置換あるいは無置換のアリール基、置換あるいは無置換の複素環基、置換アミノ基、シアノ基またはハロゲン原子を表わす。）
【００３２】
また、前記カルバゾリル基が、下記一般式［ＶＩＩ］で示されることが好ましい。
【００３３】
【化１４】
（式中、Ｒ22およびＲ23は、水素原子、置換あるいは無置換のアルキル基、置換あるいは無置換のアラルキル基、置換あるいは無置換のアリール基、置換あるいは無置換の複素環基、置換アミノ基、シアノ基またはハロゲン原子を表わし、同じであっても異なっていてもよい。）
これらの化合物のうちでも、本発明のフェナントロリン化合物は、下記一般式［Ｉ］で示されることを特徴とする。
【化１４−１】
【化１４−２】
また、下記構造式で示される化合物が好ましい。
【化１４−３】
また、本発明の有機発光素子は、陽極及び陰極からなる一対の電極と、該一対の電極間に挟持された複数の有機化合物層を有する有機発光素子において、前記複数の有機化合物層の一層が電子輸送層であり、該電子輸送層は上記フェナントロリン化合物を有することを特徴とする。
また、本発明の有機発光素子は、陽極及び陰極からなる一対の電極と、該一対の電極間に挟持された複数の有機化合物層を有する有機発光素子において、前記複数の有機化合物層の一層が発光層であり、該発光層は上記フェナントロリン化合物を有することを特徴とする。
【００３６】
【発明の実施の形態】
以下、本発明を詳細に説明する。
【００３７】
まず、本発明のフェナントロリン化合物について説明する。
【００３８】
本発明のフェナントロリン化合物は、上記一般式［Ｉ］〜［ＩＩＩ］で示され、フルオレニル基が上記一般式［ＩＶ］、フルオランテニル基が上記一般式［Ｖ］、ペリレニル基が上記一般式［ＶＩ］、カルバゾリル基が上記一般式［ＶＩＩ］で示されるものであることが好ましい。
【００３９】
上記一般式［Ｉ］〜［ＶＩＩ］における置換基の具体例を以下に示す。
【００４０】
アルキル基としては、メチル基、エチル基、ｎ−プロピル基、ｉｓｏ−プロピル基、ｎ−ブチル基、ｔｅｒ−ブチル基、オクチル基などが挙げられる。
【００４１】
アラルキル基としては、ベンジル基、フェネチル基などが挙げられる。
【００４２】
アリール基としては、フェニル基、ビフェニル基、ターフェニル基などが挙げられる。
【００４３】
複素環基としては、チエニル基、ピロリル基、ピリジル基、オキサゾリル基、オキサジアゾリル基、チアゾリル基、チアジアゾリル基、ターチエニル基などが挙げられる。
【００４４】
置換アミノ基としては、ジメチルアミノ基、ジエチルアミノ基、ジベンジルアミノ基、ジフェニルアミノ基、ジトリルアミノ基、ジアニソリルアミノ基などが挙げられる。
【００４５】
ハロゲン原子としては、フッ素、塩素、臭素、ヨウ素などが挙げられる。
【００４６】
上記置換基が有してもよい置換基としては、メチル基、エチル基、プロピル基などのアルキル基、ベンジル基、フェネチル基などのアラルキル基、フェニル基、ビフェニル基などのアリール基、チエニル基、ピロリル基、ピリジル基などの複素環基、ジメチルアミノ基、ジエチルアミノ基、ジベンジルアミノ基、ジフェニルアミノ基、ジトリルアミノ基、ジアニソリルアミノ基などのアミノ基、メトキシル基、エトキシル基、プロポキシル基、フェノキシル基などのアルコキシル基、シアノ基、フッ素、塩素、臭素、ヨウ素などのハロゲン原子などが挙げられる。
【００４７】
次に、本発明のフェナントロリン化合物の代表例を以下に挙げるが、本発明はこれらに限定されるものではない（例示化合物Ｎｏ．１，３，５が本発明の例）。
【００４８】
【化１５】
【化１６】
【化１７】
【化１８】
【化１９】
【化２０】
【化２１】
【化２２】
【化２３】
【化２４】
本発明のフェナントロリン化合物は、一般的に知られている方法で合成でき、例えば、Ｊ．Ｏｒｇ．Ｃｈｅｍ．，１６，９４１−９４５（１９５１）、Ｔｅｔｒａｈｅｄｒｏｎ，Ｌｅｔｔ．，３６，３４８９−３４９０（１９９５）などに記載の方法でフェナントロリン化合物中間体を得て、さらにパラジウム触媒を用いたｓｕｚｕｋｉ ｃｏｕｐｌｉｎｇ法（例えばＣｈｅｍ．Ｒｅｖ．１９９５，９５，２４５７−２４８３）などの合成法で得ることができる。
【００５９】
本発明のフェナントロリン化合物は、従来の化合物に比べ電子輸送性および耐久性の優れた化合物であり、有機発光素子の有機化合物を含む層、特に、電子輸送層および発光層として有用であり、また真空蒸着法や溶液塗布法などによって形成した層は結晶化などが起こりにくく経時安定性に優れている。
【００６０】
次に、本発明の有機発光素子について詳細に説明する。
【００６１】
本発明の有機発光素子は、陽極及び陰極からなる一対の電極と、該一対の電極間に狭持された一または複数の有機化合物を含む層を少なくとも有する有機発光素子において、前記有機化合物を含む層の少なくとも一層が上記一般式［Ｉ］、［ＩＩ］または［ＩＩＩ］で示されるフェナントロリン化合物の少なくとも一種を含有する。
【００６２】
本発明の有機発光素子は、有機化合物を含む層のうち少なくとも電子輸送層または発光層が、前記フェナントロリンの少なくとも一種を含有することが好ましい。
【００６３】
本発明の有機発光素子においては、上記一般式［Ｉ］〜［ＩＩＩ］で示されるフェナントロリン化合物を真空蒸着法や溶液塗布法により陽極及び陰極の間に形成する。その有機層の厚みは１０μｍより薄く、好ましくは０．５μｍ以下、より好ましくは０．０１〜０．５μｍの厚みに薄膜化することが好ましい。
【００６４】
図１〜図６に本発明の有機発光素子の好ましい例を示す。
【００６５】
図１は、本発明の有機発光素子の一例を示す断面図である。図１は、基板１上に、陽極２、発光層３及び陰極４を順次設けた構成のものである。ここで使用する発光素子は、それ自体でホール輸送能、エレクトロン輸送能及び発光性の性能を単一で有している場合や、それぞれの特性を有する化合物を混ぜて使う場合に有用である。
【００６６】
図２は、本発明の有機発光素子における他の例を示す断面図である。図２は、基板１上に、陽極２、ホール輸送層５、電子輸送層６及び陰極４を順次設けた構成のものである。この場合は、発光物質はホール輸送性かあるいは電子輸送性のいずれか、あるいは両方の機能を有している材料をそれぞれの層に用い、発光性の無い単なるホール輸送物質あるいは電子輸送物質と組み合わせて用いる場合に有用である。また、この場合、発光層は、ホール輸送層５あるいは電子輸送層６のいずれかから成る。
【００６７】
図３は、本発明の有機発光素子における他の例を示す断面図である。図３は、基板１上に、陽極２、ホール輸送層５、発光層３，電子輸送層６及び陰極４を順次設けた構成のものである。これは、キャリヤ輸送と発光の機能を分離したものであり、ホール輸送性、電子輸送性、発光性の各特性を有した化合物と適時組み合わせて用いられ、極めて材料選択の自由度が増すとともに、発光波長を異にする種々の化合物が使用できるため、発光色相の多様化が可能になる。さらに、中央の発光層３に各キャリヤあるいは励起子を有効に閉じこめて、発光効率の向上を図ることも可能になる。
【００６８】
図４は、本発明の有機発光素子における他の例を示す断面図である。図４は、図３に対して、ホール注入層７を陽極２側に挿入した構成であり、陽極２とホール輸送層５の密着性改善あるいはホールの注入性改善に効果があり、低電圧化に効果的である。
【００６９】
図５および図６は、本発明の有機発光素子における他の例を示す断面図である。図５および図６は、図３および図４に対してホールあるいは励起子（エキシトン）を陰極４側に抜けることを阻害する層（ホールブロッキング層８）を、発光層３、電子輸送層６間に挿入した構成である。イオン化ポテンシャルの非常に高い化合物をホールブロッキング層８として用いる事により、発光効率の向上に効果的な構成である。
【００７０】
ただし、図１〜図６はあくまで、ごく基本的な素子構成であり、本発明の化合物を用いた有機発光素子の構成はこれらに限定されるものではない。例えば、電極と有機層界面に絶縁性層を設ける、接着層あるいは干渉層を設ける、ホール輸送層がイオン化ポテンシャルの異なる２層から構成される、など多様な層構成をとることができる。
【００７１】
本発明に用いられる一般式［Ｉ］〜［ＩＩＩ］で示されるフェナントロリン化合物は、従来の化合物に比べ電子輸送性および耐久性の優れた化合物であり、図１〜図６のいずれの形態でも使用することができる。
【００７２】
本発明は、電子輸送層または発光層の構成成分として一般式［Ｉ］〜［ＩＩＩ］で示されるフェナントロリン化合物を用いるものであるが、これまで知られているホール輸送性化合物、発光性化合物あるいは電子輸送性化合物などを必要に応じて一緒に使用することもできる。
【００７３】
以下にこれらの化合物例を挙げる。
【００７４】
【化２５】
【化２６】
【化２７】
【化２８】
【化２９】
【化３０】
本発明の有機発光素子において、一般式［Ｉ］〜［ＩＩＩ］で示されるフェナントロリン化合物を含有する層および他の有機化合物を含有する層は、一般には真空蒸着法あるいは、適当な溶媒に溶解させて塗布法により薄膜を形成する。特に塗布法で成膜する場合は、適当な結着樹脂と組み合わせて膜を形成することもできる。
【００８１】
上記結着樹脂としては、広範囲な結着性樹脂より選択でき、たとえばポリビニルカルバゾール樹脂、ポリカーボネート樹脂、ポリエステル樹脂、ポリアリレート樹脂、ポリスチレン樹脂、アクリル樹脂、メタクリル樹脂、ブチラール樹脂、ポリビニルアセタール樹脂、ジアリルフタレート樹脂、フェノール樹脂、エポキシ樹脂、シリコーン樹脂、ポリスルホン樹脂、尿素樹脂等が挙げられるが、これらに限定されるものではない。また、これらは単独または共重合体ポリマーとして１種または２種以上混合してもよい。
【００８２】
陽極材料としては、仕事関数がなるべく大きなものがよく、例えば、金、白金、ニッケル、パラジウム、コバルト、セレン、バナジウム等の金属単体あるいはこれらの合金、酸化錫、酸化亜鉛、酸化錫インジウム（ＩＴＯ），酸化亜鉛インジウム等の金属酸化物が使用できる。また、ポリアニリン、ポリピロール、ポリチオフェン、ポリフェニレンスルフィド等の導電性ポリマーも使用できる。これらの電極物質は単独で用いてもよく、複数併用することもできる。
【００８３】
一方、陰極材料としては、仕事関数の小さなものがよく、リチウム、ナトリウム、カリウム、セシウム、カルシウム、マグネシウム、アルミニウム、インジウム、銀、鉛、錫、クロム等の金属単体あるいは複数の合金として用いることができる。酸化錫インジウム（ＩＴＯ）等の金属酸化物の利用も可能である。また、陰極は一層構成でもよく、多層構成をとることもできる。
【００８４】
本発明で用いる基板としては、特に限定するものではないが、金属製基板、セラミックス製基板等の不透明性基板、ガラス、石英、プラスチックシート等の透明性基板が用いられる。また、基板にカラーフィルター膜、蛍光色変換フィルター膜、誘電体反射膜などを用いて発色光をコントロールする事も可能である。
【００８５】
なお、作成した素子に対して、酸素や水分等との接触を防止する目的で保護層あるいは封止層を設けることもできる。保護層としては、ダイヤモンド薄膜、金属酸化物、金属窒化物等の無機材料膜、フッ素樹脂、ポリパラキシレン、ポリエチレン、シリコーン樹脂、ポリスチレン樹脂等の高分子膜、さらには、光硬化性樹脂等が挙げられる。また、ガラス、気体不透過性フィルム、金属などをカバーし、適当な封止樹脂により素子自体をパッケージングすることもできる。
【００８６】
【実施例】
以下、実施例により本発明をさらに具体的に説明していくが、本発明はこれらに限定されるものではない（合成例２、実施例１，１０，１１，１９が本発明の例）。
【００８７】
＜合成例１＞［例示化合物Ｎｏ．２の合成］
【００８８】
【化３１】
３００ｍｌ三ツ口フラスコに、２−ヨード−９，９−ジメチルフルオレン［１］５．８ｇ（１８．１ｍｍｏｌ）およびジエチルエーテル８０ｍｌを入れ、窒素雰囲気中、−７８度で攪拌下、ｎ−ブチルリチウム（１５％ヘキサン溶液）１１．７ｍｌ（１８．１ｍｍｏｌ）を滴下した。室温まで昇温し１時間攪拌した後、−２０度に冷却しバソフェナントロリン［２］１．５ｇ（４．５１ｍｍｏｌ）のトルエン１００ｍｌ分散液を滴下した。室温で１２時間攪拌後、水を加え有機層をクロロホルムで抽出し無水硫酸ナトリウムで乾燥後、アルミナカラム（ヘキサン＋クロロホルム混合展開溶媒）で精製し、例示化合物Ｎｏ．２（黄色結晶）２．４ｇ（収率７４％）を得た。
【００９０】
＜合成例２＞［例示化合物Ｎｏ．５の合成］
【００９１】
【化３２】
５００ｍｌ三ツ口フラスコに、４，７−ジブロモ−１，１０−フェナントロリン［３］*1)１．０ｇ（２．９６ｍｍｏｌ）、９，９−ジメチルフルオレン−２−ボロン酸［４］２．８ｇ（１１．８ｍｍｏｌ）、トルエン１４０ｍｌおよびエタノール７０ｍｌを入れ、窒素雰囲気中、室温で攪拌下、炭酸ナトリウム１２ｇ／水６０ｍｌの水溶液を滴下し、次いでテトラキス（トリフェニルホスフィン）パラジウム（０）０．１７ｇ（０．１５ｍｍｏｌ）を添加した。室温で３０分攪拌した後、７７度に昇温し３時間攪拌した。反応後、有機層をクロロホルムで抽出し無水硫酸ナトリウムで乾燥後、アルミナカラム（ヘキサン＋クロロホルム混合展開溶媒）で精製し、例示化合物Ｎｏ．５（白色結晶）１．５ｇ（収率９０％）を得た。
【００９３】
＜合成例３＞［例示化合物Ｎｏ．２０の合成］
【００９４】
【化３３】
３００ｍｌ三ツ口フラスコに、２−ヨード−９，９−ジメチルフルオレン［５］２．３ｇ（７．１８ｍｍｏｌ）およびジエチルエーテル６０ｍｌを入れ、窒素雰囲気中、−７８度で攪拌下、ｎ−ブチルリチウム（１５％ヘキサン溶液）４．６ｍｌ（７．１８ｍｍｏｌ）を滴下した。室温まで昇温し１時間攪拌した後、−２０度に冷却し例示化合物Ｎｏ．５ １．０ｇ（１．７７ｍｍｏｌ）のトルエン８０ｍｌ分散液を滴下した。室温で１２時間攪拌後、水を加え有機層をクロロホルムで抽出し無水硫酸ナトリウムで乾燥後、アルミナカラム（ヘキサン＋クロロホルム混合展開溶媒）で精製し、例示化合物Ｎｏ．２０（黄色結晶）１．２ｇ（収率７３％）を得た。
【００９６】
＜合成例４＞［例示化合物Ｎｏ．８の合成］
【００９７】
【化３４】
５００ｍｌ三ツ口フラスコに、３，８−ジブロモ−１，１０−フェナントロリン［６］*2)１．０ｇ（２．９６ｍｍｏｌ）、フルオランテン−８−ボロン酸［７］２．９ｇ（１１．８ｍｍｏｌ）、トルエン１４０ｍｌおよびエタノール７０ｍｌを入れ、窒素雰囲気中、室温で攪拌下、炭酸ナトリウム１２ｇ／水６０ｍｌの水溶液を滴下し、次いでテトラキス（トリフェニルホスフィン）パラジウム（０）０．１７ｇ（０．１５ｍｍｏｌ）を添加した。室温で３０分攪拌した後、７７度に昇温し３時間攪拌した。反応後、有機層をクロロホルムで抽出し無水硫酸ナトリウムで乾燥後、アルミナカラム（ヘキサン＋クロロホルム混合展開溶媒）で精製し、例示化合物Ｎｏ．８（黄色結晶）１．４ｇ（収率８２％）を得た。
【００９９】
＜実施例１＞
図３に示す構造の素子を作成した。
【０１００】
基板１としてのガラス基板上に、陽極２としての酸化錫インジウム（ＩＴＯ）をスパッタ法にて１２０ｎｍの膜厚で成膜したものを透明導電性支持基板として用いた。これをアセトン、イソプロピルアルコール（ＩＰＡ）で順次超音波洗浄し、次いでＩＰＡで煮沸洗浄後、乾燥した。さらに、ＵＶ／オゾン洗浄したものを透明導電性支持基板として使用した。
【０１０１】
透明導電性支持基板上に下記構造式で示される化合物のクロロホルム溶液をスピンコート法により３０ｎｍの膜厚で成膜し、ホール輸送層５を形成した。
【０１０２】
【化３５】
さらに下記構造式で示されるＩｒ錯体および例示化合物Ｎｏ．１で示されるフェナントロリン化合物（重量比５：１００）を真空蒸着法により２０ｎｍの膜厚で成膜し、発光層３を形成した。蒸着時の真空度は１．０×１０-4Ｐａ、成膜速度は０．２〜０．３ｎｍ／ｓｅｃの条件で成膜した。
【０１０４】
【化３６】
さらにアルミニウムトリスキノリノールを真空蒸着法により４０ｎｍの膜厚で成膜し、電子輸送層６を形成した。蒸着時の真空度は１．０×１０-4Ｐａ、成膜速度は０．２〜０．３ｎｍ／ｓｅｃの条件で成膜した。
【０１０６】
次に、陰極４として、アルミニウムとリチウム（リチウム濃度１原子％）からなる蒸着材料を用いて、上記有機層の上に真空蒸着法により厚さ５０ｎｍの金属層膜を形成し、さらに真空蒸着法により厚さ１５０ｎｍのアルミニウム層を形成した。蒸着時の真空度は１．０×１０-4Ｐａ、成膜速度は１．０〜１．２ｎｍ／ｓｅｃの条件で成膜した。
【０１０７】
さらに、窒素雰囲気中で保護用ガラス板をかぶせ、アクリル樹脂系接着材で封止した。
【０１０８】
この様にして得られた素子に、ＩＴＯ電極（陽極２）を正極、Ａｌ−Ｌｉ電極（陰極４）を負極にして、１０Ｖの直流電圧を印加すると１８．０ｍＡ／ｃｍ2の電流密度で電流が素子に流れ、４５００ｃｄ／ｍ2の輝度で緑色の発光が観測された。
【０１０９】
さらに、電流密度を６．０ｍＡ／ｃｍ2に保ち１００時間電圧を印加したところ、初期輝度８５０ｃｄ／ｍ2から１００時間後８００ｃｄ／ｍ2と輝度劣化は小さかった。
【０１１０】
＜実施例２〜９＞
例示化合物Ｎｏ．１に代えて、表１に示す例示化合物を用いた他は実施例１と同様に素子を作成し、同様な評価を行った。結果を表１に示す。
【０１１１】
＜比較例１〜３＞
例示化合物Ｎｏ．１に代えて、下記構造式で示される化合物を用いた他は実施例１と同様に素子を作成し、同様な評価を行った。結果を表１に示す。
【０１１２】
【化３７】
【表１】
＜実施例１０＞
図３に示す構造の素子を作成した。
【０１１５】
実施例１と同様に、透明導電性支持基板上にホール輸送層５を形成した。
【０１１６】
さらにクマリンおよびアルミニウムトリスキノリノール（重合比１：２０）を真空蒸着法により２０ｎｍの膜厚で成膜し、発光層３を形成した。蒸着時の真空度は１．０×１０-4Ｐａ、成膜速度は０．２〜０．３ｎｍ／ｓｅｃの条件で成膜した。
【０１１７】
さらに例示化合物Ｎｏ．３により４０ｎｍの膜厚で成膜し、電子輸送層６を形成した。蒸着時の真空度は１．０×１０-4Ｐａ、成膜速度は０．２〜０．３ｎｍ／ｓｅｃの条件で成膜した。
【０１１８】
次に、実施例１と同様にして陰極４を形成した後に封止した。
【０１１９】
この様にして得られた素子に、ＩＴＯ電極（陽極２）を正極、Ａｌ−Ｌｉ電極（陰極４）を負極にして、８Ｖの直流電圧を印加すると１１１０ｍＡ／ｃｍ2の電流密度で電流が素子に流れ、９５０００ｃｄ／ｍ2の輝度で緑色の発光が観測された。
【０１２０】
さらに、電流密度を２００ｍＡ／ｃｍ2に保ち１００時間電圧を印加したところ、初期輝度１００００ｃｄ／ｍ2から１００時間後８５００ｃｄ／ｍ2と輝度劣化は小さかった。
【０１２１】
＜実施例１１〜１８＞
例示化合物Ｎｏ．３に代えて、表２に示す例示化合物を用いた他は実施例１０と同様に素子を作成し、同様な評価を行った。結果を表２に示す。
【０１２２】
＜比較例４〜６＞
例示化合物Ｎｏ．３に代えて、比較化合物Ｎｏ．１〜３を用いた他は実施例１０と同様に素子を作成し、同様な評価を行った。結果を表２に示す。
【０１２３】
【表２】
＜実施例１９＞
図３に示す構造の素子を作成した。
【０１２５】
実施例１と同様に、透明導電性支持基板上にホール輸送層５を形成した。
【０１２６】
さらに下記構造式で示されるＩｒ錯体および下記構造式で示されるカルバゾール化合物（重合比５：１００）を真空蒸着法により２０ｎｍの膜厚で成膜し、発光層３を形成した。蒸着時の真空度は１．０×１０-4Ｐａ、成膜速度は０．２〜０．３ｎｍ／ｓｅｃの条件で成膜した。
【０１２７】
【化３８】
【化３９】
さらに例示化合物Ｎｏ．５を用い４０ｎｍの膜厚で成膜し、電子輸送層６を形成した。蒸着時の真空度は１．０×１０-4Ｐａ、成膜速度は０．２〜０．３ｎｍ／ｓｅｃの条件で成膜した。
【０１３０】
次に、実施例１と同様にして陰極４を形成した後に封止した。
【０１３１】
この様にして得られた素子に、ＩＴＯ電極（陽極２）を正極、Ａｌ−Ｌｉ電極（陰極４）を負極にして、１０Ｖの直流電圧を印加すると２０．０ｍＡ／ｃｍ2の電流密度で電流が素子に流れ、６８００ｃｄ／ｍ2の輝度で緑色の発光が観測された。
【０１３２】
さらに、電流密度を６．０ｍＡ／ｃｍ2に保ち１００時間電圧を印加したところ、初期輝度１３００ｃｄ／ｍ2から１００時間後１１５０ｃｄ／ｍ2と輝度劣化は小さかった。
【０１３３】
＜実施例２０〜３１＞
例示化合物Ｎｏ．５に代えて、表３に示す例示化合物を用いた他は実施例１９と同様に素子を作成し、同様な評価を行った。結果を表３に示す。
【０１３４】
＜比較例７〜９＞
例示化合物Ｎｏ．５に代えて、比較化合物Ｎｏ．１〜３を用いた他は実施例１９と同様に素子を作成し、同様な評価を行った。結果を表３に示す。
【０１３５】
【表３】
【発明の効果】
以上説明のように、一般式［Ｉ］〜［ＩＩＩ］で示されるフェナントロリン化合物を用いた有機発光素子は、低い印加電圧で高輝度な発光が得られ、耐久性にも優れている。特に本発明のフェナントロリン化合物を含有する有機層は、電子輸送層として優れ、かつ発光層としても優れている。
【０１３７】
さらに、素子の作成も真空蒸着あるいはキャステイング法等を用いて作成可能であり、比較的安価で大面積の素子を容易に作成できる。
【図面の簡単な説明】
【図１】本発明における有機発光素子の一例を示す断面図である。
【図２】本発明における有機発光素子の他の例を示す断面図である。
【図３】本発明における有機発光素子の他の例を示す断面図である。
【図４】本発明における有機発光素子の他の例を示す断面図である。
【図５】本発明における有機発光素子の他の例を示す断面図である。
【図６】本発明における有機発光素子の他の例を示す断面図である。
【符号の説明】
１ 基板
２ 陽極
３ 発光層
４ 陰極
５ ホール輸送層
６ 電子輸送層
７ ホール注入層
８ ホール／エキシトンブロッキング層[0001]
BACKGROUND OF THE INVENTION
The present invention relates to a novel organic compound and an organic light-emitting device using the same.
[0002]
[Prior art]
An organic light-emitting device has a fluorescent compound or a phosphorescent compound by injecting electrons and holes from each electrode by sandwiching a thin film containing a fluorescent organic compound or a phosphorescent organic compound between an anode and a cathode. This is an element that utilizes the light emitted when the exciton is generated and the exciton returns to the ground state.
[0003]
In 1987, Kodak Research (Non-patent Document 1) used ITO for the anode and magnesium-silver alloy for the cathode, an aluminum quinolinol complex as the electron transport material and the light emitting material, and a triphenylamine derivative as the hole transport material. The device having the function-separated type two-layer structure used has been reported to emit about 1000 cd / m 2 at an applied voltage of about 10V. Examples of related patents include
[0004]
Further, by changing the type of the fluorescent organic compound, light emission from ultraviolet to infrared is possible, and recently, various compounds have been actively researched. For example, it describes in patent documents 4-11.
[0005]
In recent years, many studies have been made on using phosphorescent compounds as light emitting materials and using triplet state energy for EL light emission. A group of Princeton University reports that an organic light emitting device using an iridium complex as a light emitting material exhibits high luminous efficiency (Non-Patent Document 2).
[0006]
Furthermore, in addition to the organic light-emitting device using the low-molecular material as described above, an organic light-emitting device using a conjugated polymer has been reported by a group of Cambridge University (Non-Patent Document 3). In this report, light emission was confirmed in a single layer by forming a film of polyphenylene vinylene (PPV) in a coating system.
[0007]
Patents 12 to 16 and the like can be cited as related patents of organic light emitting devices using conjugated polymers.
[0008]
As described above, recent advances in organic light-emitting devices are remarkable, and their features are high brightness, variety of emission wavelengths, high-speed response, low profile, and light-emitting devices with low applied voltage. Suggests the possibility to.
[0009]
However, under the present circumstances, light output with higher brightness or higher conversion efficiency is required. In addition, there are still many problems in terms of durability, such as changes over time due to long-term use and deterioration due to atmospheric gas containing oxygen or moisture. Furthermore, it is necessary to emit blue, green, and red light with good color purity when considering application to a full color display or the like, but these problems are still not sufficient.
[0010]
On the other hand, phenanthroline compounds are used as electron transport materials and light-emitting materials because of their excellent electron transport properties. Examples of using a phenanthroline compound in an organic light emitting device include Patent Documents 17 to 21 and the like, but characteristics when used as a light emitting layer material or an electron transport material are not sufficient.
[0011]
[Patent Document 1]
US Pat. No. 4,539,507 [Patent Document 2]
US Pat. No. 4,720,432 [Patent Document 3]
US Pat. No. 4,885,211 [Patent Document 4]
US Pat. No. 5,151,629 [Patent Document 5]
US Pat. No. 5,409,783 [Patent Document 6]
US Pat. No. 5,382,477 [Patent Document 7]
JP-A-2-247278 [Patent Document 8]
JP-A-3-255190 [Patent Document 9]
JP-A-5-202356 [Patent Document 10]
Japanese Patent Laid-Open No. 9-202878 [Patent Document 11]
JP-A-9-227576 [Patent Document 12]
US Pat. No. 5,247,190 [Patent Document 13]
US Pat. No. 5,514,878 [Patent Document 14]
US Pat. No. 5,672,678 [Patent Document 15]
JP-A-4-145192 [Patent Document 16]
JP-A-5-247460 [Patent Document 17]
JP-A-5-331459 [Patent Document 18]
JP-A-7-82551 [Patent Document 19]
JP-A-10-79297 [Patent Document 20]
JP 2001-267080 A [Patent Document 21]
JP 2001-131174 A [Non-Patent Document 1]
Appl. Phys. Lett. 51,913 (1987)
[Non-Patent Document 2]
Nature, 395, 151 (1998)
[Non-Patent Document 3]
Nature, 347, 539 (1990)
[0012]
[Problems to be solved by the invention]
An object of the present invention is to provide a novel phenanthroline compound.
[0013]
Another object of the present invention is to provide an organic light-emitting device using a specific phenanthroline compound and having an extremely high efficiency and high luminance light output.
[0014]
Another object of the present invention is to provide an extremely durable organic light emitting device.
[0015]
It is another object of the present invention to provide an organic light emitting device that is easy to manufacture and can be produced at a relatively low cost.
[0016]
[Means for Solving the Problems]
That is, the phenanthroline compound of the present invention is represented by any one of the following general formulas [I] to [III].
[0017]
[Chemical 8]
(Wherein R 1 , R 2 , R 3 , R 4 , R 5 and R 6 are a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, A substituted or unsubstituted heterocyclic group or a halogen atom, which may be the same or different, Ar 1 and Ar 2 are a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted fluoranthenyl group, It represents a substituted or unsubstituted perylenyl group or a substituted or unsubstituted carbazolyl group, which may be the same or different.
[0019]
[Chemical 9]
Wherein R 7 , R 8 , R 9 , R 10 , R 11 and R 12 are a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, A substituted or unsubstituted heterocyclic group or a halogen atom, which may be the same or different, Ar 3 and Ar 4 are a substituted or unsubstituted fluorenyl group, a substituted or unsubstituted fluoranthenyl group, It represents a substituted or unsubstituted perylenyl group or a substituted or unsubstituted carbazolyl group, which may be the same or different.
[0021]
[Chemical Formula 10]
(Wherein R 13 , R 14 , R 15 and R 16 are each a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted complex, R 13 and R 14 may be the same or different, Ar 5 , Ar 6 , Ar 7 and Ar 8 are substituted or unsubstituted fluorenyl groups, substituted or unsubstituted A substituted fluoranthenyl group, a substituted or unsubstituted perylenyl group or a substituted or unsubstituted carbazolyl group, which may be the same or different;
[0023]
In the phenanthroline compound of the present invention, the fluorenyl group is preferably represented by the following general formula [IV].
[0024]
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(In the formula, R 17 represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted amino group, or a cyano group. R 18 and R 19 each represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, or a substituted or unsubstituted heterocyclic group. , May be the same or different.)
[0026]
Moreover, it is preferable that the said fluoranthenyl group is shown by the following general formula [V].
[0027]
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(Wherein R 20 represents a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted amino group, or a cyano group. Or represents a halogen atom.)
[0029]
The perylenyl group is preferably represented by the following general formula [VI].
[0030]
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Wherein R 21 is a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, a substituted amino group, or a cyano group. Or represents a halogen atom.)
[0032]
The carbazolyl group is preferably represented by the following general formula [VII].
[0033]
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Wherein R 22 and R 23 are a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted heterocyclic group, or a substituted amino group. A cyano group or a halogen atom, which may be the same or different.
Among these compounds, the phenanthroline compound of the present invention is represented by the following general formula [I].
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Moreover, the compound shown by the following structural formula is preferable.
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Further, the organic light-emitting device of the present invention comprises a pair of electrodes composed of an anode and a cathode, the organic light emitting element which have a organic compound layer of the number of double sandwiched between the pair of electrodes, the plurality of organic compound layers more is an electron-transporting layer, electron transporting layer is characterized by chromatic said phenanthroline compound.
The organic light-emitting device of the present invention includes a pair of electrodes composed of an anode and a cathode, and a plurality of organic compound layers sandwiched between the pair of electrodes. It is a light emitting layer, This light emitting layer has the said phenanthroline compound, It is characterized by the above-mentioned.
[0036]
DETAILED DESCRIPTION OF THE INVENTION
Hereinafter, the present invention will be described in detail.
[0037]
First, the phenanthroline compound of the present invention will be described.
[0038]
The phenanthroline compound of the present invention is represented by the above general formulas [I] to [III], the fluorenyl group is the above general formula [IV], the fluoranthenyl group is the above general formula [V], and the perylenyl group is the above general formula [ VI] and the carbazolyl group are preferably those represented by the above general formula [VII].
[0039]
Specific examples of the substituents in the general formulas [I] to [VII] are shown below.
[0040]
Examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an iso-propyl group, an n-butyl group, a ter-butyl group, and an octyl group.
[0041]
Examples of the aralkyl group include a benzyl group and a phenethyl group.
[0042]
Examples of the aryl group include a phenyl group, a biphenyl group, and a terphenyl group.
[0043]
Examples of the heterocyclic group include thienyl group, pyrrolyl group, pyridyl group, oxazolyl group, oxadiazolyl group, thiazolyl group, thiadiazolyl group, and tertenyl group.
[0044]
Examples of the substituted amino group include a dimethylamino group, a diethylamino group, a dibenzylamino group, a diphenylamino group, a ditolylamino group, and a dianisolylamino group.
[0045]
Examples of the halogen atom include fluorine, chlorine, bromine and iodine.
[0046]
Examples of the substituent that the substituent may have include an alkyl group such as a methyl group, an ethyl group, and a propyl group, an aralkyl group such as a benzyl group and a phenethyl group, an aryl group such as a phenyl group and a biphenyl group, a thienyl group, Heterocyclic groups such as pyrrolyl group and pyridyl group, amino groups such as dimethylamino group, diethylamino group, dibenzylamino group, diphenylamino group, ditolylamino group, and dianisolylamino group, methoxyl group, ethoxyl group, propoxyl group, Examples include alkoxyl groups such as phenoxyl groups, cyano groups, halogen atoms such as fluorine, chlorine, bromine and iodine.
[0047]
Next, typical examples of the phenanthroline compound of the present invention are listed below, but the present invention is not limited to these (Exemplary Compound Nos . 1, 3, and 5 are examples of the present invention) .
[0048]
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The phenanthroline compound of the present invention can be synthesized by a generally known method. Org. Chem. 16, 941-945 (1951), Tetrahedron, Lett. , 36, 3489-3490 (1995), etc. to obtain a phenanthroline compound intermediate, and further a synthesis method such as Suzuki coupling method using a palladium catalyst (for example, Chem. Rev. 1995, 95, 2457-2483). Can be obtained at
[0059]
The phenanthroline compound of the present invention is a compound excellent in electron transportability and durability as compared with conventional compounds, and is useful as a layer containing an organic compound of an organic light emitting device, in particular, as an electron transport layer and a light emitting layer. A layer formed by a vapor deposition method or a solution coating method is less likely to be crystallized and has excellent temporal stability.
[0060]
Next, the organic light emitting device of the present invention will be described in detail.
[0061]
The organic light-emitting device of the present invention includes the organic compound in an organic light-emitting device having at least a layer including a pair of electrodes composed of an anode and a cathode and one or more organic compounds sandwiched between the pair of electrodes. At least one of the layers contains at least one phenanthroline compound represented by the above general formula [I], [II] or [III].
[0062]
In the organic light emitting device of the present invention, it is preferable that at least the electron transport layer or the light emitting layer among the layers containing an organic compound contains at least one of the phenanthrolines.
[0063]
In the organic light-emitting device of the present invention, the phenanthroline compound represented by the general formulas [I] to [III] is formed between the anode and the cathode by a vacuum deposition method or a solution coating method. The thickness of the organic layer is less than 10 μm, preferably 0.5 μm or less, more preferably 0.01 to 0.5 μm.
[0064]
1 to 6 show preferred examples of the organic light emitting device of the present invention.
[0065]
FIG. 1 is a cross-sectional view showing an example of the organic light emitting device of the present invention. FIG. 1 shows a structure in which an
[0066]
FIG. 2 is a cross-sectional view showing another example of the organic light emitting device of the present invention. FIG. 2 shows a configuration in which an
[0067]
FIG. 3 is a cross-sectional view showing another example of the organic light emitting device of the present invention. FIG. 3 shows a structure in which an
[0068]
FIG. 4 is a cross-sectional view showing another example of the organic light emitting device of the present invention. FIG. 4 shows a configuration in which a
[0069]
5 and 6 are cross-sectional views showing other examples of the organic light-emitting device of the present invention. 5 and FIG. 6 show a layer (hole blocking layer 8) that prevents holes or excitons (excitons) from passing to the
[0070]
However, FIG. 1 to FIG. 6 are very basic device configurations, and the configuration of the organic light emitting device using the compound of the present invention is not limited thereto. For example, various layer configurations such as providing an insulating layer at the interface between the electrode and the organic layer, providing an adhesive layer or an interference layer, and the hole transport layer including two layers having different ionization potentials can be employed.
[0071]
The phenanthroline compounds represented by the general formulas [I] to [III] used in the present invention are superior in electron transportability and durability compared to conventional compounds, and can be used in any form of FIGS. can do.
[0072]
In the present invention, the phenanthroline compound represented by the general formulas [I] to [III] is used as a constituent component of the electron transport layer or the light emitting layer. An electron transporting compound or the like can be used together as necessary.
[0073]
Examples of these compounds are given below.
[0074]
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In the organic light-emitting device of the present invention, the layer containing the phenanthroline compound represented by the general formulas [I] to [III] and the layer containing another organic compound are generally dissolved in a vacuum deposition method or an appropriate solvent. A thin film is formed by a coating method. In particular, when a film is formed by a coating method, the film can be formed in combination with an appropriate binder resin.
[0081]
The binder resin can be selected from a wide range of binder resins such as polyvinyl carbazole resin, polycarbonate resin, polyester resin, polyarylate resin, polystyrene resin, acrylic resin, methacrylic resin, butyral resin, polyvinyl acetal resin, diallyl phthalate. Resins, phenol resins, epoxy resins, silicone resins, polysulfone resins, urea resins and the like can be mentioned, but are not limited thereto. Moreover, you may mix these 1 type, or 2 or more types as a single or copolymer polymer.
[0082]
As the anode material, one having a work function as large as possible is preferable. For example, simple metals such as gold, platinum, nickel, palladium, cobalt, selenium, vanadium or alloys thereof, tin oxide, zinc oxide, indium tin oxide (ITO) Metal oxides such as zinc indium oxide can be used. In addition, conductive polymers such as polyaniline, polypyrrole, polythiophene, and polyphenylene sulfide can also be used. These electrode materials may be used alone or in combination.
[0083]
On the other hand, the cathode material preferably has a small work function, and can be used as a single metal or a plurality of alloys such as lithium, sodium, potassium, cesium, calcium, magnesium, aluminum, indium, silver, lead, tin, and chromium. it can. A metal oxide such as indium tin oxide (ITO) can also be used. Further, the cathode may have a single layer structure or a multilayer structure.
[0084]
Although it does not specifically limit as a board | substrate used by this invention, Transparent substrates, such as opaque board | substrates, such as a metal board | substrate and a ceramic board | substrate, glass, quartz, a plastic sheet, are used. It is also possible to control the color light by using a color filter film, a fluorescent color conversion filter film, a dielectric reflection film, or the like on the substrate.
[0085]
Note that a protective layer or a sealing layer can be provided on the prepared element for the purpose of preventing contact with oxygen or moisture. Examples of protective layers include diamond thin films, inorganic material films such as metal oxides and metal nitrides, polymer films such as fluororesins, polyparaxylene, polyethylene, silicone resins, and polystyrene resins, and photocurable resins. Can be mentioned. Further, it is possible to cover glass, a gas impermeable film, a metal, etc., and to package the element itself with an appropriate sealing resin.
[0086]
【Example】
Hereinafter, the present invention will be described more specifically with reference to examples. However, the present invention is not limited to these examples (Synthesis Example 2, Examples 1, 10, 11, and 19 are examples of the present invention) .
[0087]
<Synthesis Example 1> [Exemplary Compound No. 1] Synthesis of 2]
[0088]
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A 300 ml three-necked flask was charged with 5.8 g (18.1 mmol) of 2-iodo-9,9-dimethylfluorene [1] and 80 ml of diethyl ether, and stirred under a nitrogen atmosphere at -78 degrees under n-butyllithium (15 % Hexane solution) 11.7 ml (18.1 mmol) was added dropwise. After raising the temperature to room temperature and stirring for 1 hour, the mixture was cooled to −20 ° C., and a toluene dispersion of 1.5 g (4.51 mmol) of bathophenanthroline [2] was added dropwise. After stirring at room temperature for 12 hours, water was added, the organic layer was extracted with chloroform, dried over anhydrous sodium sulfate, and purified with an alumina column (hexane + chloroform mixed developing solvent). 2.4 g (yield 74%) of 2 (yellow crystals) was obtained.
[0090]
<Synthesis Example 2> [Exemplary Compound No. 2] Synthesis of 5]
[0091]
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In a 500 ml three-necked flask, 4,7-dibromo-1,10-phenanthroline [3] * 1) 1.0 g (2.96 mmol), 9,9-dimethylfluorene-2-boronic acid [4] 2.8 g (11) 0.8 mmol), 140 ml of toluene, and 70 ml of ethanol were added dropwise under stirring at room temperature in a nitrogen atmosphere, and then an aqueous solution of 12 g of sodium carbonate / 60 ml of water was added dropwise, and then 0.17 g of tetrakis (triphenylphosphine) palladium (0) (0. 15 mmol) was added. After stirring at room temperature for 30 minutes, the temperature was raised to 77 degrees and stirred for 3 hours. After the reaction, the organic layer was extracted with chloroform, dried over anhydrous sodium sulfate, and purified with an alumina column (hexane + chloroform mixed developing solvent). 5 (white crystals) 1.5 g (yield 90%) was obtained.
[0093]
<Synthesis Example 3> [Exemplary Compound No. Synthesis of 20]
[0094]
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A 300 ml three-necked flask was charged with 2.3 g (7.18 mmol) of 2-iodo-9,9-dimethylfluorene [5] and 60 ml of diethyl ether, and stirred under a nitrogen atmosphere at -78 degrees under n-butyllithium (15 4.6% (7.18 mmol) was added dropwise. After raising the temperature to room temperature and stirring for 1 hour, the mixture was cooled to -20 degrees and exemplified Compound No. 5 A 1.0 ml (1.77 mmol) 80 ml toluene dispersion was added dropwise. After stirring at room temperature for 12 hours, water was added, the organic layer was extracted with chloroform, dried over anhydrous sodium sulfate, and purified with an alumina column (hexane + chloroform mixed developing solvent). Thus, 1.2 g (yield 73%) of 20 (yellow crystals) was obtained.
[0096]
<Synthesis Example 4> [Exemplary Compound No. Synthesis of 8]
[0097]
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In a 500 ml three-necked flask, 3,8-dibromo-1,10-phenanthroline [6] * 2) 1.0 g (2.96 mmol), fluoranthene-8-boronic acid [7] 2.9 g (11.8 mmol), toluene 140 ml of ethanol and 70 ml of ethanol were added, and an aqueous solution of 12 g of sodium carbonate / 60 ml of water was added dropwise with stirring in a nitrogen atmosphere at room temperature, and then 0.17 g (0.15 mmol) of tetrakis (triphenylphosphine) palladium (0) was added. . After stirring at room temperature for 30 minutes, the temperature was raised to 77 degrees and stirred for 3 hours. After the reaction, the organic layer was extracted with chloroform, dried over anhydrous sodium sulfate, and purified with an alumina column (hexane + chloroform mixed developing solvent). 1.4 g (yield 82%) of 8 (yellow crystals) was obtained.
[0099]
<Example 1>
An element having the structure shown in FIG. 3 was prepared.
[0100]
What formed indium tin oxide (ITO) as an
[0101]
A hole transport layer 5 was formed by depositing a chloroform solution of a compound represented by the following structural formula on a transparent conductive support substrate with a film thickness of 30 nm by spin coating.
[0102]
Embedded image
Furthermore, Ir complexes represented by the following structural formulas and Exemplified Compound Nos. The light-emitting
[0104]
Embedded image
Furthermore, aluminum triskinolinol was formed into a film with a thickness of 40 nm by a vacuum deposition method, and the
[0106]
Next, a metal layer film having a thickness of 50 nm is formed on the organic layer by a vacuum deposition method using a deposition material composed of aluminum and lithium (lithium concentration: 1 atomic%) as the
[0107]
Further, a protective glass plate was placed in a nitrogen atmosphere and sealed with an acrylic resin adhesive.
[0108]
When a direct current voltage of 10 V was applied to the device obtained in this manner with the ITO electrode (anode 2) as the positive electrode and the Al-Li electrode (cathode 4) as the negative electrode, a current density of 18.0 mA / cm 2 was applied. And green light emission was observed at a luminance of 4500 cd / m 2 .
[0109]
Further, when a voltage was applied for 100 hours with the current density kept to 6.0 mA / cm 2, after the initial luminance 850 cd / m 2 100 hours 800 cd / m 2 and luminance degradation was small.
[0110]
<Examples 2 to 9>
Exemplified Compound No. A device was prepared in the same manner as in Example 1 except that the exemplified compounds shown in Table 1 were used in place of 1, and the same evaluation was performed. The results are shown in Table 1.
[0111]
<Comparative Examples 1-3>
Exemplified Compound No. A device was prepared in the same manner as in Example 1 except that a compound represented by the following structural formula was used instead of 1, and the same evaluation was performed. The results are shown in Table 1.
[0112]
Embedded image
[Table 1]
<Example 10>
An element having the structure shown in FIG. 3 was prepared.
[0115]
In the same manner as in Example 1, a hole transport layer 5 was formed on a transparent conductive support substrate.
[0116]
Furthermore, coumarin and aluminum triskinolinol (polymerization ratio 1:20) were formed into a film with a thickness of 20 nm by a vacuum evaporation method, and the
[0117]
Furthermore, Exemplified Compound No. 3 was formed to a film thickness of 40 nm to form an
[0118]
Next, the
[0119]
When a direct current voltage of 8 V was applied to the device thus obtained with an ITO electrode (anode 2) as a positive electrode and an Al-Li electrode (cathode 4) as a negative electrode, a current was generated at a current density of 1110 mA / cm 2. And emission of green light was observed at a luminance of 95000 cd / m 2 .
[0120]
Further, when a voltage was applied for 100 hours while keeping the current density at 200 mA / cm 2 , the luminance deterioration was small, from an initial luminance of 10000 cd / m 2 to 8500 cd / m 2 after 100 hours.
[0121]
<Examples 11 to 18>
Exemplified Compound No. A device was prepared in the same manner as in Example 10 except that the exemplified compounds shown in Table 2 were used instead of 3, and the same evaluation was performed. The results are shown in Table 2.
[0122]
<Comparative Examples 4-6>
Exemplified Compound No. In place of Comparative compound No. 3 Elements were prepared in the same manner as in Example 10 except that 1 to 3 were used, and the same evaluation was performed. The results are shown in Table 2.
[0123]
[Table 2]
<Example 19>
An element having the structure shown in FIG. 3 was prepared.
[0125]
In the same manner as in Example 1, a hole transport layer 5 was formed on a transparent conductive support substrate.
[0126]
Further, an Ir complex represented by the following structural formula and a carbazole compound (polymerization ratio 5: 100) represented by the following structural formula were formed into a film with a thickness of 20 nm by a vacuum deposition method, whereby the
[0127]
Embedded image
Embedded image
Furthermore, Exemplified Compound No. 5 was used to form an
[0130]
Next, the
[0131]
When a direct current voltage of 10 V was applied to the device thus obtained with a positive electrode of the ITO electrode (anode 2) and a negative electrode of the Al-Li electrode (cathode 4), a current density of 20.0 mA / cm 2 was applied. And green light emission was observed at a luminance of 6800 cd / m 2 .
[0132]
Further, when a voltage was applied for 100 hours while keeping the current density at 6.0 mA / cm 2 , the luminance deterioration was small, from the initial luminance of 1300 cd / m 2 to 1150 cd / m 2 after 100 hours.
[0133]
<Examples 20 to 31>
Exemplified Compound No. A device was prepared in the same manner as in Example 19 except that the exemplified compounds shown in Table 3 were used in place of 5, and the same evaluation was performed. The results are shown in Table 3.
[0134]
<Comparative Examples 7-9>
Exemplified Compound No. In place of Comparative compound No. 5 Elements were prepared in the same manner as in Example 19 except that 1 to 3 were used, and the same evaluation was performed. The results are shown in Table 3.
[0135]
[Table 3]
【The invention's effect】
As described above, the organic light-emitting device using the phenanthroline compounds represented by the general formulas [I] to [III] can emit light with high luminance at a low applied voltage and has excellent durability. In particular, the organic layer containing the phenanthroline compound of the present invention is excellent as an electron transport layer and also excellent as a light emitting layer.
[0137]
Furthermore, the element can also be formed by using vacuum deposition or a casting method, and an element having a relatively large area can be easily formed.
[Brief description of the drawings]
FIG. 1 is a cross-sectional view showing an example of an organic light emitting device in the present invention.
FIG. 2 is a cross-sectional view showing another example of the organic light emitting device according to the present invention.
FIG. 3 is a cross-sectional view showing another example of the organic light emitting device according to the present invention.
FIG. 4 is a cross-sectional view showing another example of the organic light emitting device in the present invention.
FIG. 5 is a cross-sectional view showing another example of the organic light emitting device in the present invention.
FIG. 6 is a cross-sectional view showing another example of the organic light emitting device in the present invention.
[Explanation of symbols]
DESCRIPTION OF
Claims (6)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002272408A JP4261855B2 (en) | 2002-09-19 | 2002-09-19 | Phenanthroline compound and organic light emitting device using the same |
| PCT/JP2003/011485 WO2004026870A1 (en) | 2002-09-19 | 2003-09-09 | Phenanthroline compound and organic light emitting device using same |
| US10/527,192 US7550594B2 (en) | 2002-09-19 | 2003-09-09 | Phenanthroline compound and organic light emitting device using same |
| AU2003260955A AU2003260955A1 (en) | 2002-09-19 | 2003-09-09 | Phenanthroline compound and organic light emitting device using same |
| US12/436,507 US7982213B2 (en) | 2002-09-19 | 2009-05-06 | Phenanthroline compound and organic light emitting device using same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2002272408A JP4261855B2 (en) | 2002-09-19 | 2002-09-19 | Phenanthroline compound and organic light emitting device using the same |
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| Publication Number | Publication Date |
|---|---|
| JP2004107263A JP2004107263A (en) | 2004-04-08 |
| JP4261855B2 true JP4261855B2 (en) | 2009-04-30 |
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| JP2002272408A Expired - Fee Related JP4261855B2 (en) | 2002-09-19 | 2002-09-19 | Phenanthroline compound and organic light emitting device using the same |
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| Country | Link |
|---|---|
| US (2) | US7550594B2 (en) |
| JP (1) | JP4261855B2 (en) |
| AU (1) | AU2003260955A1 (en) |
| WO (1) | WO2004026870A1 (en) |
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| JP4729776B2 (en) * | 2000-08-04 | 2011-07-20 | 東レ株式会社 | Light emitting element |
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| WO2004026870A1 (en) | 2004-04-01 |
| US7550594B2 (en) | 2009-06-23 |
| US20060097227A1 (en) | 2006-05-11 |
| US20090218940A1 (en) | 2009-09-03 |
| AU2003260955A1 (en) | 2004-04-08 |
| US7982213B2 (en) | 2011-07-19 |
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